2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl azide

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl azide
• CAS No.: 94427-00-6
• Molecular Formula: C14H19 N3 O9
• Molecular Weight: 373.32
• DSSTox Substance ID: DTXSID10461082
• Nikkaji Number: J1.506.421H
• Mol file: 94427-00-6.mol

Synonyms:94427-00-6;2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl azide;[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-azidooxan-2-yl]methyl acetate;2,3,4,6-TETRA-O-ACETYL-ALPHA-D-GALACTOPYRANOSYL AZIDE;DTXSID10461082;(2R,3S,4S,5R,6S)-2-[(Acetyloxy)methyl]-6-azidooxane-3,4,5-triyl triacetate (non-preferred name)

Chemical Property of 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl azide

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 373.11212919
• Heavy Atom Count: 26
• Complexity: 617

Purity/Quality:

98%min ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl azide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C
• Uses: 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl Azide can be applied toward anti-tumor drugs and anti-hepatitis B virus.

Technology Process of 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl azide

There total 2 articles about 2,3,4,6-Tetra-O-acetyl-a-D-galactopyranosyl azide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0) → azido-2,3,4,6-tetra-O-acetyl-1-deoxy-α-D-galactopyranose (94427-00-6)

Guidance literature:

With sodium azide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/bc100394k

Reference yield: 44.0%

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0) → azido-2,3,4,6-tetra-O-acetyl-1-deoxy-α-D-galactopyranose (94427-00-6) + (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-26-2)

Guidance literature:

With tetrabutylammoniun azide; In tetrahydrofuran; for 60h; Reflux;

DOI:10.1016/j.bmcl.2010.04.151

Reference yield: 97.0%

benzaldehyde (100-52-7) + azido-2,3,4,6-tetra-O-acetyl-1-deoxy-α-D-galactopyranose (94427-00-6) → 1-N-benzylidene-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)imine

Guidance literature:

azido-2,3,4,6-tetra-O-acetyl-1-deoxy-α-D-galactopyranose; With trimethylphosphane; In dichloromethane; at 20 ℃; for 0.25h;

benzaldehyde; In dichloromethane; at 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)00380-5

upstream raw materials:

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl chloride

Downstream raw materials:

1-N-benzoyl-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)amine

2,3,4-Tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-galactopyranosylazid

2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylamine

C₄₄H₆₃N₇O₁₇

Refernces

• 1、 Slamova, Kristyna,Marhol, Petr,Bezouska, Karel,Lindkvist, Lise,Hansen, Signe G.,Kren, Vladimir,Jensen, Henrik H.. "Synthesis and biological activity of glycosyl-1H-1,2,3-triazoles". supporting information; experimental part. p. 4263 - 4265. Retrieved 2010/08/22.